Functionalised pyrrolidinones derived from (S)-pyroglutamic acid
1996; Elsevier BV; Volume: 52; Issue: 10 Linguagem: Inglês
10.1016/0040-4020(96)00047-6
ISSN1464-5416
AutoresMark Beard, Jonathan H. Bailey, David T. Cherry, Mark G. Moloney, Sung Bo Shim, Kathryn A Statham, Mark J. Bamford, R. B. LAMONT,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoThe generation of the lactam enolate derived from bicyclic lactams 2a-c, prepared from (S)-pyroglutamic acid 1a, and subsequent reaction with a range of electrophiles, is reported. Exo-diastereoselectivity is generally favoured. The deprotection of some of these adducts to give functionalised hydroxymethylpyrrolidinones is readily achieved by simple hemiaminal ether cleavage under acidic conditions.
Referência(s)